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The Retirement Wisdom Podcast

The Retirement Wisdom Podcast

By: Retirement Wisdom
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 Retire SmarterRetirement Wisdom LLC Personal Development Personal Success
Episodes
  • Can I Retire Yet? – Darrow Kirkpatrick

    Can I Retire Yet? – Darrow Kirkpatrick
    Feb 23 2026
    Don’t drift into retirement. Design yours. Learn more about our next small group coaching program starting in April here. Sign up here. Very Early Registration Discount ends on March 1st. _______________________ What happens when you finally get everything you worked for…and realize something is missing? In this powerful and deeply honest conversation, Darrow Kirkpatrick shares what early retirement can really feel like — beyond the spreadsheets and freedom headlines. After leaving his software engineering career, he found himself confronting something he didn’t expect: the loss of identity and clout that work had quietly provided. He discovered that early retirement wasn’t just about having time—it was about creating meaning. Instead of retreating, Darrow leaned into challenges. From launching a successful retirement blog Can I Retire Yet? to spending nights alone above 12,000 feet, to confronting his lifelong struggles with fear and panic, Darrow’s journey, chronicled in his new book Two Sticks, One Path, reveals the surprising truth about what can make retirement fulfilling. If you’re within a few years of retirement — or already there — this conversation will make you think differently about what comes next – and why the challenges we choose to take on may matter more than the comfort we think we want. _________________________ Bio Darrow Kirkpatrick is the author of the new book Two Sticks, One Path: A Journey Beyond Fear on the Colorado Trail. Darrow is an early-retired civil and software engineer with five decades of hiking, biking, and technical rock-climbing experience, including first ascents in the Shawangunks of New York and the sandstone belt of Tennessee. He climbed three big walls in Yosemite Valley, California: The Shield and The Nose on El Capitan, and The Regular Northwest Face of Half Dome. In 2011 he founded “Can I Retire Yet?” — winner of the 2019 Plutus award for Best Retirement Blog. His personal finance books include “Retiring Sooner” and “Can I Retire Yet?” ___________________________ For More on Darrow Kirkpatrick Two Sticks, One Path: A Journey Beyond Fear on the Colorado Trail Can I Retire Yet? ___________________________ Podcast Conversations You May Like How to Prepare Mentally for Life After Work – Joseph Maugeri The Inspired Retirement – Nathalie Martin Lessons Learned in Early Retirement – Chris Mamula _____________________________ About The Retirement Wisdom Podcast There are many podcasts on retirement, often hosted by financial advisors with their own financial motives, that cover the money side of the street. This podcast is different. You’ll get smarter about the investment decisions you’ll make about the most important asset you’ll have in retirement: your time. About Retirement Wisdom I help people who are retiring, but aren’t quite done yet, discover what’s next and build their custom version of their next life. A meaningful retirement doesn’t just happen by accident. Schedule a call today to discuss how the Designing Your Life process created by Bill Burnett & Dave Evans can help you make your life in retirement a great one — on your own terms. About Your Podcast Host Joe Casey is an executive coach who helps people design their next life after their primary career and create their version of The Multipurpose Retirement.™ He created his own next chapter after a 26-year career at Merrill Lynch, where he was Senior Vice President and Head of HR for Global Markets & Investment Banking. Joe has earned Master’s degrees from the University of Southern California in Gerontology (at age 60), the University of Pennsylvania, and Middlesex University (UK), a BA in Psychology from the University of Massachusetts at Amherst, and his coaching certification from Columbia University. In addition to his work with clients, Joe hosts The Retirement Wisdom Podcast, ranked in the top 1% globally in popularity by Listen Notes, with over 1.6 million downloads. Business Insider recognized Joe as one of 23 innovative coaches who are making a difference. He’s the author of Win the Retirement Game: How to Outsmart the 9 Forces Trying to Steal Your Joy. ___________________________ Wise Quotes On the Value of Challenge in Retirement “I find 100% of the meaning that I found in early retirement has come from the challenges I’ve tackled.” On Meaningful Pursuits “The things I did pay attention to starting Can I Retire Yet, a successful personal finance blog, a bucket list item hiking the Colorado Trail, even though I had to do most of it on crutches, those things are incredibly meaningful to me, writing a memoir about it. I think I would have really regretted if I had stayed at my corporate desk through all those years instead of reaching for those bucket list items.” On Adaptation “I did have a series of chronic injuries in my lower body, which got worse. I had a bad hamstring injury, was in bed for a few months, ...
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    25 mins
  • Retire with Purpose – Cesar Aguirre

    Retire with Purpose – Cesar Aguirre
    Feb 16 2026
    Will you retire with purpose? Don’t leave it to chance. Design Your New Life after you leave full-time work. Learn more about our next small group coaching program starting in April here – and sign up here. __________________________ What if the word retirement is setting us up for the wrong life? After years in senior leadership roles, Cesar Aguirre discovered something most of us miss about retirement: the word itself matters more than we think. In English, we “retire” – we withdraw. In Portuguese, you become “aposentado” – left aside or left behind. But in Spanish-speaking cultures, retirement is called “jubilación” – which comes from the word for joy. That distinction changed everything for Cesar. Because when he stepped away from his career, it wasn’t the loss of work that shocked him – it was the jarring shock of losing an identity. He realized retirement isn’t just a life transition, it’s an identity transition, offering an opportunity to redefine who you want to become, and retire with purpose. Cesar joins us to share the framework he developed through his own transition – a ten-chapter roadmap for moving from “what I’m leaving” to “what I’m moving toward.” He’ll reveal why planning goes far beyond your finances, how to measure success when you’re no longer producing output, and the key warning signs that show up early when retirement first starts going wrong. This is a conversation about why approaching retirement with more intention might just create the most fulfilling chapters of your life. How will you retire with purpose? Cesar Aguirre joins us from Florida. __________________________ Bio César Aguirre is a seasoned HR executive with over 40 years of experience in global talent development. Now in active retirement, he embodies reinvention with passion as mentor, consultant, and author. In his book, Retirement with Purpose: The 10 Rs of Retirement, he shares his vibrant energy and insights to help readers rediscover purpose and embrace joyful living in their post-career lives. He currently resides in a lively 55+ community in Central Florida with his wife, inspiring others to design their authentic journeys for the second act of their lives. _______________________ For More on Cesar Aguirre Retirement with Purpose: The 10 Rs of Retirement _______________________ Podcast Conversations You May Like How to Prepare Mentally for Life After Work – Joseph Maugeri Re-Visioning Retirement – Susan Reid, PhD How to Retire – Christine Benz _________________________ About The Retirement Wisdom Podcast There are many podcasts on retirement, often hosted by financial advisors with their own financial motives, that cover the money side of the street. This podcast is different. You’ll get smarter about the investment decisions you’ll make about the most important asset you’ll have in retirement: your time. About Retirement Wisdom I help people who are retiring, but aren’t quite done yet, discover what’s next and build their custom version of their next life. A meaningful retirement doesn’t just happen by accident. Schedule a call today to discuss how the Designing Your Life process created by Bill Burnett & Dave Evans can help you make your life in retirement a great one — on your own terms. About Your Podcast Host Joe Casey is an executive coach who helps people design their next life after their primary career and create their version of The Multipurpose Retirement.™ He created his own next chapter after a 26-year career at Merrill Lynch, where he was Senior Vice President and Head of HR for Global Markets & Investment Banking. Joe has earned Master’s degrees from the University of Southern California in Gerontology (at age 60), the University of Pennsylvania, and Middlesex University (UK), a BA in Psychology from the University of Massachusetts at Amherst, and his coaching certification from Columbia University. In addition to his work with clients, Joe hosts The Retirement Wisdom Podcast, ranked in the top 1% globally in popularity by Listen Notes, with over 1.6 million downloads. Business Insider recognized Joe as one of 23 innovative coaches who are making a difference. He’s the author of Win the Retirement Game: How to Outsmart the 9 Forces Trying to Steal Your Joy. _________________________ Wise Quotes On The Power of Language “Retirement becomes a celebration, not a retreat. I think the languages shape mindset. And mindsets shape behavior. So when retirement is framed as a joy, planning shifts from survival to flourishing become more natural.” On Measuring Success in Retirement “A good day is no longer about output, it’s no longer about how much you produce. It’s about action that is intended, an action that aligns with a master plan.” On What He’d Do Differently “I wish I had thought about it and prepared for my post-work identity a little sooner and more deliberately. In my job in HR, I helped many ...
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    30 mins
  • How to Live a Meaningful Life – Dave Evans

    How to Live a Meaningful Life – Dave Evans
    Feb 9 2026
    Sign up for our next Designing Your Life small group coaching program starting in April here __________________________ What happens when you’ve done everything “right” — built a successful career, made a difference, checked the boxes — and yet something still is missing? Today I’m joined by Dave Evans, co-author of How to Live a Meaningful Life: Using Design Thinking to Unlock Purpose, Joy, and Flow Every Day and the #1 New York Times Bestseller Designing Your Life, and a longtime Stanford educator, to explore a question many people quietly wrestle with in the second half of life: Why doesn’t impact bring lasting meaning — and what actually does? Dave shares insights from his newest work with Bill Burnett on meaning, presence, and what he calls the shift from role to soul. We talk about why chasing fulfillment often backfires, why the most meaningful moments are often small and fleeting, and how many of us live almost entirely in what he calls the “transactional world” — often missing the richness of the present moment that’s available right now. This conversation is especially relevant if you’re nearing retirement, newly retired, or simply sensing that achievement alone isn’t enough anymore. Dave offers practical reframes, deeply human stories, and a powerful idea he calls the scandal of particularity — a concept that may completely change how you think about what a well-lived life really looks like. Dave Evans joins us from California to discuss How to Live a Meaningful Life. ___________________________ Bio Dave Evans is the co-author of How to Live a Meaningful Life: Using Design Thinking to Unlock Purpose, Joy, and Flow Every Day. Dave has worked in alternative energy, telecommunications, and high tech. As an early member of the advanced systems group that built the technology that became the Macintosh, he led the first computer mouse team and laser-printing projects, before leaving to co-found the software giant Electronic Arts. After more than thirty years of executive leadership and management consulting in the high tech world, Evans realized that what he really wanted and needed to do was help people rediscover purpose in their jobs and lives. He joined Stanford’s Design Program, teaching the incredibly popular Designing Your Life course. In their book Designing Your Life, Dave Evans and co-author Bill Burnett, brought these principles to a larger audience, proving it’s never too late to design a life you love through innovation, creative problem-solving, and a growth mindset. Evans teaches audiences of all ages that the same principles used to create amazing technology and products can also be used to design and build a life filled with purpose and joy that is constantly creative and productive. Dave Evans earned a Bachelors of Science and Masters of Science in Mechanical Engineering from Stanford and a graduate diploma in Contemplative Spirituality from San Francisco Theological Seminary. He lives in Santa Cruz. _________________________ For More on Dave Evans How to Live a Meaningful Life: Using Design Thinking to Unlock Purpose, Joy, and Flow Every Day Design Your Life and Get Unstuck – Dave Evans (2020 Podcast) _________________________ Podcast Conversatons You May Like The Good Life – Marc Schulz, PhD Resurface – Cassidy Krug The Purpose Code – Dr. Jordan Grumet __________________________ About The Retirement Wisdom Podcast There are many podcasts on retirement, often hosted by financial advisors with their own financial motives, that cover the money side of the street. This podcast is different. You’ll get smarter about the investment decisions you’ll make about the most important asset you’ll have in retirement: your time. About Retirement Wisdom I help people who are retiring, but aren’t quite done yet, discover what’s next and build their custom version of their next life. A meaningful retirement doesn’t just happen by accident. Schedule a call today to discuss how the Designing Your Life process created by Bill Burnett & Dave Evans can help you make your life in retirement a great one — on your own terms. About Your Podcast Host Joe Casey is an executive coach who helps people design their next life after their primary career and create their version of The Multipurpose Retirement.™ He created his own next chapter after a 26-year career at Merrill Lynch, where he was Senior Vice President and Head of HR for Global Markets & Investment Banking. Joe has earned Master’s degrees from the University of Southern California in Gerontology (at 60), the University of Pennsylvania, and Middlesex University (UK), a BA in Psychology from the University of Massachusetts at Amherst, and his coaching certification from Columbia University. In addition to his work with clients, Joe hosts The Retirement Wisdom Podcast, ranked in the top 1% globally in popularity by Listen Notes, with over 1.9 million downloads. Business Insider ...
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    47 mins
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